


A proper learning experience

by Shitfacedanon



Category: Homestuck
Genre: Anal Play, Anal Sex, F/M, Femdom, Pegging
Language: English
Status: Completed
Published: 2013-01-29
Updated: 2013-01-29
Packaged: 2017-11-27 09:34:27
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,477
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/660418
Author URL: https://archiveofourown.org/users/Shitfacedanon/pseuds/Shitfacedanon
Summary: <blockquote class="userstuff">
              <p>While John Egbert certainly possesses both the enthusiasm and willingness to try to please his partner, his overall technique however could do with some work. Luckily he has just the perfect teacher to help guide him along.</p>
            </blockquote>





	A proper learning experience

**Author's Note:**

> This was a collaboration between http://nicks-ass.tumblr.com/ and I, he doesn't own a AO3 account so I'm posting that info here.

John felt nervous; a girl was in his room, and not just any girl but a girl he really liked. A pretty, cute, smart, and charming girl by the name of Rose lalonde. The two had known each other for years, and while before John had always considered Rose nothing more than a friend (despite whatever erotic dreams and personal fantasies might suggest otherwise) as he came of age he had to admit to feeling a certain more than platonic attraction to her. Whenever Rose laughed at his jokes he felt his heart skip a beat. Whenever she touched him, even accidentally, he missed the feeling of her skin against his. Whenever she would walk, John would notice himself staring at her modest chest and correct himself; so ungentlemanly of him, why what would his father think of such behavior? Then again it was never really Rose’ bosom that caught his attention, but instead that curvy plush rump of hers. 

How John loved every aspect of it, how it was just the right size. Not too big like some of the exaggerated porn stars he would occasionally ogle. But not too small either. It was basically perfect, how each ass cheek jiggled and bounced with each step, how it had the exactly perfect curve that set his loins afire. Why if John was Shakespeare he’d compose entire epics all in honor of Rose’ ass. How they would articulate how each cheek was likely to be tight and firm enough not to sag, but still loose enough to be fun to play with. Like the kind of ass cheeks one could slap and tease with, perhaps even rest their head against. The kind of ass one would love to hotdog with, or maybe if one were feeling rather adventurous, perhaps even toss a salad or two with. Yes, truly Rose Lalonde had a posterior to envy.  
Of course, John was not Shakespeare; he wasn’t even a writer. Anyone could admire that round heart shaped mound. He was a horny sixteen year old boy with the girl of his dreams sitting in his room asking him what the hell he was doing. John flashed back to reality and mumbled an apology. Rose chuckled mischievously and told him, “It’s why I like you John, there’s something so adorably goofy about you.” Well, at least it was a complement, John thought. “Do you know what else I like about you John?” Rose asked, John shaking his head ignorantly. “I like that you’re more honest than most guys. I like how you’re fully willing to toss banter right back without coming off like as asshole.” John blushed at her words. Rose started to walk toward John seductively, slightly exaggerating every sway of her hips as she started to pull her shirt off. “But you want to know what I really like about you John?” Rose said as she pressed her chest against John. 

His eyes hovered on her black lace bra and then darted guiltily to her face. John had to swallow before he could reply, "no, what?"

“I love how you know how to really admire a nice ass John.” Rose responded as she snatched John’s hands up and guided them decisively to her rump. “I like how you really appreciate a good ass. Most men just glimpse at it, John! They glimpse at it and that’s it. It’s always the tits that grab their attention.” John continued to stare at Rose, not sure what to make of this. “It's never the ass. You must know that most pornographic material focuses on the chest, John, but there's always been this secondary interest in the ass.” Rose pressed his hands into her rump, forcing him to squeeze and rub it as a bit of disdain entered her voice. “Why is that John? Why only the tits? The ass has so much more to offer. You could give a man a tit job, but you can also let a man hotdog his cock between your cheeks and let him cum all over your back. But can a chest be fucked, John? Can it?” Rose asked, raising her eyebrow and giving him a smug look. John remained silent, not sure if he should reply, his hands moving without her guidance now.

“No, but he can fuck an ass. And why not? Why not John?” She gave him an appraising look, then placed both of her hands on her skirt. As she pulled it off, she whispered a question into John's ear: "Why don’t you fuck my ass?” John hesitated, removing his hands and wondering what to make of this situation. He was usually the one on the receiving end of these things, and finally being offered a chance to pitch for once felt alien to him. How did one really go about fucking an ass? All his partners had always seemed to know either instinctively or through experience what to do, pounding him in all the right ways. Was it as simple as that that? Well, he thought, there was a first time for everything, and Rose could always guide him. “yes rose, i’ll fuck your ass.” 

Rose's smile widened. "John, I've been waiting for this for a long time. Even when I was a young girl, I always had a curious mind. Once when I was reading a more salacious wizard tale than the ones I've showed you, I thought to experiment with my ass and, well, John, to make a long story short, I’ve been a fan of the feeling ever since. John, I can think of no better person to take my black cherry after all this time.” 

John felt his pants tighten; imagining Rose shoving all manner of objects up her ass made his dick rock hard. Thoughts of Rose in the shower, using a brush or or some other phallic object to get herself off filled his head. His imagination didn't stop there. Maybe, when her mother was gone, Rose would ride some fruit and vegetable in the kitchen before her mother returned. Or maybe Rose would, after several weeks of practice and stretching, slip an entire hand into her ass and pretend it was her sweet pony Maplehoof fucking her. John's personal fantasies were interrupted a second time by Rose, this time with an exasperated expression on her face and absolutely nothing on her body. “John, are you going to fuck me or what?” How did she get so fast?

John giggled nervously and began to pull his pants off, his stiff cock eager to penetrate. “I'm glad at least part of you is paying attention.” Rose said, her smirk returning. She bent and beckoned John over, spreading her cheeks as he drew near. John knew what to do! He was the ass master, it was him. He rubbed himself against Rose, teasing her. He began to push himself into her before being interrupted. “John! What the hell are you doing back there?” Rose asked. 

“i’m trying to fuck you like you want,” he offered. Did he really mess up already?

She gave John a dumbfounded look. “John. There is more to fucking an ass then just jumping in there; you have to ease into it. Are you really that clueless about this?” 

“well... whenever i’m on the receiving end of things, there’s usually nothing like that, nope. i mean, usually vriska or kanaya or jade just bend me over and just shove it in.” He had no idea that was unusual.

Rose's surprise and her sexual frustration were making her more careless with her speech than she normally was. “John, not everyone is an anal whore like you are! Some of us prefer having a little foreplay and preparation before moving on to the main attraction.” She turned to raise her eyebrows at John. “Really, even Jade?” He nodded, smiling at the memory. It had been good.

Rose pulled his shirt on and told John to sit tight. “It looks as if I’m going to have to teach you some etiquette. Allow me to gather some tools; I'll return momentarily.” Sure enough, a few minutes later Rose was back with an impressive array of dildos, a strap-on harness, and a small bottle. Rose dumped toys on his bed and was nude again in a flash. “Get undressed and bend over.” She told him. He didn’t need to ask her where she was going with this; he was very familiar with how things worked from this side. John obeyed, stripping down and positioning himself with his hands on one of his dressers and his legs spread. “Now, John, I’m going to be your sex ed teacher today,“ she said, starting to get into the role.

Rose grabbed the bottle of lube, squirted a small dab on her fingertip, and smeared it up her finger. “Now lesson one: foreplay and stimulation. It's best to ease into these things. You need to be gradual about it and gently work your way up.” Rose slowly eased her finger in John's ass. He moaned quietly. He was used to the merciless pounding the other girls liked, but this was different. He had his doubts at first, but Rose’s soft teasing was coaxing out that familiar warm pleasurable feeling. “Now, John, once you start the experience, it’s important to build up upon it. For example, by adding girth.” Rose withdrew her finger and reached for the bottle again, this time slathering her entire hand with the stuff while John watched. 

“Don’t worry, John, I did say I would build up to things. It would be a shame if I were to jump the proverbial gun on this. Consider this a preparation of sorts.” Rose slowly pushed back into him, this time with two fingers. She started to pump them into him, occasionally varying her pace, but always slowing down if he seemed to be enjoying it too much. John wanted to jerk off, but Rose stopped him, telling him that she wouldn’t let her student ruin his own education. Every time he stepped out of line, Rose ground her fingers against his prostate for a few seconds, leaving him gasping and helpless to object.

Rose added another finger, maintaining that same slow, teasing pace of hers. She knew that John desperately wanted her to shove her whole fist in, but she was in no rush to comply. She still had so many toys to use, and it would be such a waste if John got off so early in the proceedings. Once she felt she could easily fit her entire hand in, she pulled all her fingers out entirely. “Now, John, time for lesson two: sex toys and stimulation.” Rose informed him. 

She picked up a toy from the bed and showed it to him. “Now, student, do you know what this is?” He looked from it to Rose, trying to figure out what she was holding. She smiled when it became clear that he wouldn't figure it out. “A prostate massager, John, a very fun and entertaining little thing. Why don't we try it? And remember John. No jerking, no cumming. I'll take care of that." John nodded. 

Rose eased the toy into John, enjoying his squirming as she teased him. When she finally had the entire length in she finally touched his cock, stroking him gently. She tweaked the toy, moving it just enough to make John moan and squirm. Then she increased the speed of her strokes, pumping him faster and faster and grinding her toy into him more firmly. Whenever she felt the little shudders that meant he was close to climaxing, she would ease up on her efforts and let him relax before picking up speed again. 

Rose's lesson continued for a few more minutes, grinding and jerking John off at an uneven rate that never gave him release. It was a learning experience, after all, and if John was ever going to learn to satisfy Rose, he needed to know how much fun anal could be. What better way was there to teach than pushing the gasping and squealing boy to his limit? She continued pushing her toy against John prostate. Every she thought he was about to finish, she firmly grasped his dick to prevent it. Their lesson plan may have been almost finished, but it would be a shame if it ended before she could get to the finals.  
Feeling satisfied with the circumstances Rose then gently pulled the toy free from John’s now loose ass. She walked back to the bed and in a flash had her strap on at the ready. Reaching for the lube, she spread a generous amount over it and returned to her eager student.  
Placing one hand on John's hip and another on her toy she slowly shoved the head of the dildo into his ass. Unsurprisingly she met no resistance and managed to get the entire cock into John. John moaned as she did, his own dick twitching slightly in arousal. Rose slowly pulled her toy out, then more firmly then before, pushed back in, eliciting a louder moan from the boy. With every successive thrust she increased the force and speed, bucking against John. Every time getting a even louder and more lustful moan or grunt from him. As she slammed against him, Rose could feel a bump against her own privates. Though not enough to properly stimulate her, it was enough to get her horny. And now wanting to enjoy a little action herself, Rose stopped caring about teaching John anything. Grasping John's hips as hard as she could she began to pound him in earnest, viciously yanking him back, trying desperately to get herself off now. Rose continued to relentlessly slam against John, now yelping in ecstasy at every thrust, small drips of precum falling from his cock. Rose herself getting hornier with each bump against her, now completely unaware of her pupil.

Exhaustively she continued to pound and slam John, inching closer and closer to her own little orgasm while John begged her to never stop. With one final ounce of strength she thrusted as hard as she could, finally feeling her body seize up in pleasure while John struggled to hold himself up as he also came.

Exhausted, Rose lazily removed the dildo from John and after ditching it walked to the bed, she tossed her other remaining toys aside, clearing the surface and collapsed into the bed. John joined her and after adjusting herself the two began to cuddle affectionately. 

"And now my star pupil, I believe I can say with full confidence that you passed. And with flying colors." John pressed his head against hers. "well i did learn from the best." Exhausted and tired the two then fell into a deep sleep and dreamed of all sorts of new fun.


End file.
